Phosphorus oxychloride → 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

HRID 2386680Notes

Reaction equation

HRID 2386680 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418413HCID 178418413, compound

Product 1

HCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Procedure

A mixture of 4-hydroxy-2-methylsulfanyl-pyrimidine-5-carbonitrile (2.76 g) and phosphorus oxychloride (15 mL) was heated at reflux, under argon atmosphere, for 3 h. The reaction mixture was cooled and then evaporated under reduced pressure. Hexane was added to the residue and the mixture was heated at reflux, the resulting mixture was decanted and the same procedure was repeated for 4 times. The combined supernatant layers were evaporated to afford 1.13 g of 4-chloro-2-methylsulfanyl-pyrimidine-5-carbonitrile as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux, under argon atmosphere, for 3 h
  3. temperatureThe reaction mixture was cooled
  4. customevaporated under reduced pressure
  5. additionHexane was added to the residue
  6. temperaturethe mixture was heated
  7. temperatureat reflux
  8. customthe resulting mixture was decanted
  9. customThe combined supernatant layers were evaporated

Sources & evidence

ORD record
ord-dab1a00453aa4938bb09f46b4c5a5566
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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